CH603750A5 - Azo dispersion dyes contg. thiophene gps. - Google Patents

Azo dispersion dyes contg. thiophene gps.

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Publication number
CH603750A5
CH603750A5 CH869976A CH869976A CH603750A5 CH 603750 A5 CH603750 A5 CH 603750A5 CH 869976 A CH869976 A CH 869976A CH 869976 A CH869976 A CH 869976A CH 603750 A5 CH603750 A5 CH 603750A5
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Switzerland
Prior art keywords
alkyl
sep
hydrogen
formula
alkoxy
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CH869976A
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German (de)
Inventor
Peter Dr Matzinger
Original Assignee
Sandoz Ag
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Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH869976A priority Critical patent/CH603750A5/en
Publication of CH603750A5 publication Critical patent/CH603750A5/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3608—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom
    • C09B29/3613—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom from an indole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3643—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from quinolines or hydrogenated quinolines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3678—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only oxygen as heteroatom

Abstract

Azo dispersion dyes of formula (I) are claimed in which R1 is H opt. substd. alkyl or phenyl, -COR3, -SO2R3 or -CONR4R'4, R2 and R'2 are H, CN, NO2, COR'3 or SO2R3, R3 is opt. substd. alkyl or phenyl, alkoxy or phenoxy. R'3 is OH or as for R3, R4 is H, alkyl or phenyl, R'4 is H or alkyl and K is the residue of a coupling component of the benzene naphthalene or heterocyclic series or a cpd. with an activated methylene gp, and the mol. is free from sulphonic acid gps.The (I) are made by coupling the diazonium deriv. of a cpd. (II) with a cpd. H-K.The dyes (I) can be applied from aq. dispersion to textile materials e.g. of linear aromatic polyesters, cellulose 2 1/2 and 3-acetate and synthetic polyamides to give fast yellow, red, orange, violet etc. shades with excellent resistance to light, thermal fixing, sublimation and pleating.

Description

  

  
 



   Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Azo-Dispersionsfarbstoffen.



   Die neuen Dispersionsfarbstoffe entsprechen der Formel I
EMI1.1     
 worin   Rl    Wasserstoff, gegebenenfalls substituiertes Alkyl oder Phenyl oder eine Gruppe der Formel -COR3, -SO2R3 oder   -CO-NR4RI4,    R2 und R'2 unabhängig voneinander Wasserstoff, Cyan, Nitro oder eine Gruppe der Formel -CO-R'3 oder -SO2-R3, die Symbole R3 unabhängig voneinander gegebenenfalls substituiertes Alkyl oder Phenyl, Alkoxy oder Phenoxy, die Symbole R'3 unabhängig voneinander Hydroxyl oder eine der Bedeutungen von R3, R4 Wasserstoff, Alkyl oder Phenyl,   Rt4    Wasserstoff oder Alkyl, und K den Rest einer Kupplungskomponente der Benzol-, Naphthalin- oder heterocyclischen Reihe oder aus der Reihe der Verbindungen mit aktivierter Methylengruppe bedeuten und das Molekül von Sulfonsäuregruppen frei ist.



  Unabhängig von den übrigen Symbolen bzw. Substituenten, bedeuten vorzugsweise:   Rl    Wasserstoff,   Cl-4-Alkyl,    das einen Substituenten aus der Gruppe Chlor, Brom, Cyan oder   Cl-4-Alkoxy-carbonyl    tragen kann,   Cl-4-Alkyl-carbonyl,      Cl-Alkoxy-carbonyl,    Cl-2-Alkylaminocarbonyl,   Di-(C1-2-alkyl)-aminocarbonyl,      Cl-2-Alkylsul-    fonyl,   Cl-2-Alkoxysulfonyl    oder Phenylsulfonyl, insbesondere Wasserstoff; R2 und R'2   Cl-2-Alkoxy-carbonyl    oder Cyan, insbesondere   Cl-2-Alkoxy-carbonyl;

  ;    K den Rest einer Kupplungskomponente der Aminobenzol-, Aminonaphthalin-, Pyrazolon-5-, 5-Aminopyrazol-, Pyridon-, Pyrimidon-, Phenol-, Naphthol-, Diaminopyridin-, Diaminopyrimidin-, Tetrahydrochinolin-, Cumarin- oder Pyrrolreihe oder aus der Gruppe der Verbindungen mit aktivierter Methylengruppe, insbesondere einen Rest der Formel IV
EMI1.2     
   Rs    Wasserstoff oder einen gegebenenfalls substituierten   C1-    Alkylrest, insbesondere Wasserstoff oder einen   Cl-4-Alkylrest,    der gegebenenfalls einen Substituenten aus der Gruppe Cyan, Chlor, Hydroxyl,   Cl-2-Alkoxy,    Formyloxy, Chloracetoxy,   C1-    Alkyl-carbonyloxy,   Cl-2-Alkoxy-carbonyl,      Cl-2-Alkoxy-carbo-    nyloxy und Benzoyloxy trägt, vor allem C2-3-Alkyl,

   das durch Cyan oder   Cl-2-Alkyl-carbonyloxy    substituiert ist; R6 einen gegebenenfalls substituierten   Cl-4-Alkyl-    oder Phenylrest, insbesondere einen   Cl-4-Alkylrest,    der gegebenenfalls einen Substituenten aus der Reihe Hydroxy,   Cl-2-Alkoxy,    Cyan, Phenyl, Phenoxy, Formyloxy, Chloracetoxy,   Cl-4-Alkyl-    carbonyloxy,   Cl-2-Alkoxy-carbonyl,      Cl-2-Alkoxy-carbonyloxy,    Benzoyloxy, Phenylaminocarbonyloxy, Phthalimidyl, Saccharinyl-2, Pyridyl oder Benzthiazolyl-2-mercapto trägt, oder einen Phenylrest, der gegebenenfalls ein oder zwei Substituenten aus der Gruppe Chlor, Brom, Methyl, Methoxy und Äthoxy trägt, vor allem C2-3-Alkyl, das durch   Cl-2-Alkyl-carbonyloxy    substituiert ist,

   oder Rs und R6 zusammen einen gegebenenfalls durch eine -0-   oder -SOz-Brücke    unterbrochenen Alkylenrest; R7 Wasserstoff, Chlor, Brom, Cyan,   Cl-2-Alkyl,      Cl-2-Alkoxy    oder einen Acylaminorest, insbesondere Wasserstoff, Chlor, Brom, Cyan, Methyl,   Cl-2-Alkoxy,    Formylamino,   Cl-4-Alkyl-    carbonylamino, Benzoylamino, Chlor-, Brom- oder Phenoxyalkylcarbonylamino,   Cl-l-Alkoxycarbonylamino,    Benzyloxy-carbonylamino, G-2-Alkoxy-äthoxycarbonylamino oder   G-2-Alkylsulfonylamino,    vor allem Wasserstoff, Methyl oder   Cí-2-Alkyl-carbonylamino;    Rs Wasserstoff, Methyl, Chlor, Brom,   Cl-2-Alkoxy    oder Phenoxy, insbesondere Wasserstoff.



   Vorzugsweise bedeuten R7 und Rs nicht gleichzeitig Chlor oder Brom.



   Als Acylreste in Acylamino (R7) sind vorzugsweise Reste der Formel R-Y- oder   R'-D    zu verstehen, darin bedeuten R Alkyl, das einen Substituenten aus der Gruppe Chlor, Brom, Hydroxyl, Alkoxy, Cyan, Phenyl, Phenoxy, Amino, Alkyloder Dialkylamino und Phenylamino tragen kann oder Phenyl, das bis zu zwei Substituenten aus der Gruppe Chlor, Brom, Methyl, Methoxy, Nitro, Cyan und Alkoxycarbonyl tragen kann, Y ein Radikal der Formel -O-CO- oder -S02-, R' Wasserstoff oder eine der Bedeutungen von R, Z ein Radikal der Formel -CO-, -NR/'CO- oder -NR"SO2und   R"    Wasserstoff oder eine der Bedeutungen von R, wobei jedoch Acetale ausgeschlossen sind.



   Als Acylaminoreste kommen insbesondere Formylamino, Alkylcarbonylamino, Chlor-, Brom-, Alkoxy-, Phenyl-, Phenoxy- oder Cyan-alkylcarbonylamino, Alkoxy-carbonylamino, Alkoxy-äthoxy- oder -propoxy-carbonylamino, Alkylsulfonylamino und Benzoylamino, worin der Benzolkern einen Substituenten aus der Gruppe Chlor, Brom, Methyl, Methoxy, Nitro und Cyan tragen kann, in Betracht.



   Sofern nicht anders angegeben, enthalten alle Alkylreste (und auch die Alkoxyreste) 1, 2, 3 oder 4, insbesondere 1 oder 2 Kohlenstoffatome.



   Das Verfahren zur Herstellung der neuen Verbindungen der Formel   list    dadurch gekennzeichnet, dass man die Diazoniumverbindung aus einem Amin der Formel II
EMI1.3     
 mit einer Verbindung der Formel III
H-K (III) kuppelt.



   Die Amine der Formel II sind bekannt, sie werden z. B. von G. Gompper et al., Annalen 659, 90-101, (1962), beschrieben, bzw, lassen sich analog zu bekannten Methoden herstellen.



   Die Herstellung der Diazoniumverbindungen und das Kuppeln mit den Verbindungen der Formel III erfolgt ebenfalls analog zu bekannten Methoden.



   Die Verarbeitung der neuen Verbindungen der Formel I zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z. B.



  durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken. Die Farbstoffe ziehen aus wässriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hoch  molekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern, sowie aus Cellulose-2 1/2acetat, Cellulose-triacetat und synthetischen Polyamiden.



   Man färbt oder bedruckt nach an sich bekannten, z. B. dem in der französischen Patentschrift Nr. 1 445 371 beschriebenen Verfahren.



   Die erhaltenen Färbungen besitzen gute Allgemeinechtheiten; hervorzuheben sind die Lichtechtheit, die Thermofixier-, Sublimier- und Plissierechtheit.



   In den folgenden Beispielen bedeuten die Teile Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben.



   Beispiel 1
Zu einem Gemisch aus 107 Teilen Nitrosylschwefelsäure (hergestellt durch Auflösen von 7 Teilen Natriumnitrit in 100 Teilen konzentrierter Schwefelsäure), 85 Teilen Eisessig und 15 Teilen Propionsäure werden bei   0-5     langsam 31,5 Teile 3   Amino-4-hydroxy-thieno-[2,3-b]-thiophen-dicarbonsäure-(2,-    5)-diäthylester zugegeben. Das erhaltene Gemisch wird bei 05o mit einer Mischung aus 85 Teilen Eisessig und 15 Teilen Propionsäure versetzt und anschliessend während 3 Stunden bei   0-5o    gerührt. 

  Hierauf tropft man eine Lösung von 28,9 Teilen N-(2'-Acetoxyäthyl)-N-(2'-cyanäthyl)-aminobenzol in 85 Teilen Eisessig und 15 Teilen Propionsäure zu und rührt das resultierende Kupplungsgemisch während 3 Stunden bei   0-5O.    Hierauf giesst man das Reaktionsgemisch unter Rühren zu einer Mischung aus 600 Teilen Eis und 300 Teilen Wasser, wobei der entstandene Farbstoff ausfällt. Er wird abfiltriert, mit Wasser   säure-    und salzfrei gewaschen und getrocknet. Der so erhaltene Farbstoff färbt synthetische Fasern in roten Tönen mit ausgezeichneten Echtheiten.



   In den folgenden Tabellen sind weitere, analog zur Arbeitsweise des obigen Beispiels herstellbare, neue Dispersionsfarbstoffe und die Nuance ihrer Ausfärbungen auf Polyesterfasermaterial angegeben.  



     Tabelle 1      Farbstoffe der Formel:   
EMI3.1     
   Bsp.No. R1 R2 R'2 R5 R6 R7 R8 Nuance auf Polyester 2 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H rubin 3 H -COOCH3 -COOCH3 -CH2CH2-OCOCH3 -CH2CH2CN H H rot 4 H -COOC2H5 -COOC2H5 -CH2CH2-OCOCH3 -CH2CH2OCOCH3 -NHCOC2H5 H rubin 5 H -COOC2H5 -COOC2H5 -CH2CH2-OCOCH3 -CH2CH2CN -NHCOCH3 H rot 6 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2OCONHC6H5 H H rot 7 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2OC6H5 H H rot 8 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN H H rot 9 H -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 -NHCOCH3 -OC2H5 violett 10 H -COOC2H5 -COOC2H5 -C2H5 -C2H5 -NHCOCH3 H violett 11 H -COOC2H5 -COOC2H5 H -CH2CH2COOC2H5 -NHCOCH3 H rot 12 H -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 H rot 13 H -COOC2H5 -COOC2H5 -CH2CH2CN -CH2CH2COOCH3 H H rot 14 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2OCONHC6H5 -CH3 H rubin 

   15 H -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 H H rot 16 H -COOC2H5 -COOC2H5 CH2CH2CN -CH2CH2OH H H rot 17 H -COOC2H5 -COOC2H5 H -CH2CH2OCOCH3 -OCH3 -OCH3 rot 18 H -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -OCH3 -OCH3 rot 19 H -COOC2H5 -COOC2H5 H -CH2CH2OCOCH3 -NHCOCH3 Cl rot 20 H -COOC2H5 -COOC2H5 H -CH2CH2OCOOCH3 -NHCOCH3 Cl rot 21 H -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 Cl rot 22 H -COOC2H5 -COOC2H5 -C2H5 -C2H5 -NHCOOCH2 H violett CH2OC2H5 23 H -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 -OC2H5 violett 24 H -COOCH(CH3)2 -COOCH(CH3)2 -CH2CH2OCOCH3 -CH2CH2CN H H rot 25 H -COOCH(CH3)2 -COOCH(CH3)2 -C2H5 -CH2CH2CN -CH3 H rubin 26 H -COOCH(CH3)2 -COOCH(CH3)2 -CH2CH2COOCH3 -CH2CH2CN H H rot 27 H -COOCH(CH3)2 -COOCH(CH3)2 -C2H5 -CH2CH2OCONHC6H5 -CH3 H rubin 28 H -COOCH(CH3)2 -COOCH(CH3)2 -C2H5 -CH2CH2CN H H rot 29 H -CN -CN -CH2CH2OCOCH3 -CH2CH2CN H H rubin 30 H -CN -CN -C2H5 -CH2CH2OC6H5 

   H H violett 31 H -CN -CN -C2H5 -CH2CH2CN H H violett 32 H -CN -CN H -CH2CH2COOC2H5 H H rubin 33 H -CN -CN -C2H5 -CH2CH2OCONHC6H5 H H rubin 34 H -CN -CN -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H rot 35 H -CON(CH3)2 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H rot 36 H -CON(CH3)2 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN H H rot        Tabelle 1 (Fortsetzung) Bsp.No.

  R1 R2 R'2 R5 R6 R7 R8 Nuance auf Polyester 37 H -CON(CH3)2 -COOC2H5 -C2H5 -CH2CH2CN H H rubin 38 H -CONHCH3 -COOC2H5 -C2H5 -CH2CH2OCOCH3 H H rubin 39 H -CONHCH3 -COOC2H5 H -CH2CH2COOC2H5 H H rubin 40 H -CONH2 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H rubin 41 H -CONH2 -COOC2H5 H -CH2CH2OCOCH3 -NHCOCH3 Cl violett 42 H -CN -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 -NHCOC2H5 H rubin 43 H -CN -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN H H rot 44 H -CN -COOC2H5 -C2H5 -CH2CH2CN H H rubin 45 H -CN -COOC2H5 H -CH2CH2COOC2H5 H rubin 46 H -CN -COOC2H5 H -CH2CH2OCOCH3 -OCH3 -OCH3 rot 47 H -CN -COOC2H5 H -CH2CH2COOCH3 -OCH3 -OCH3 rot 48 H -CN -COOC2H5 -C2H5 -CH2CH2OC6H5 H H violett 49 CH3CO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H orange 50 CH3CO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN H H orange 51 CH3CO- -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 H rot 52 CH3OCO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H 

   scharlach 53 CH3OCO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN H H scharlach 54 CH3OCO- -COOC2H5 -COOC2H5 -C2H5 -C2H5 -NHCOCH3 H rot 55 CH3OCO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2OC6H5 H H rot 56 CH3OCO- -COOC2H5 -COOC2H5 H -CH2CH2COOC2H5 -NHCOCH3 H rot 57 (CH3)2NCO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H rot 58 (CH3)2NCO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 -NHCOC2H5 H scharlach 59 CH3SO2- -COOC2H5 -COOC2H5 -C2H5 -C2H5 -NHCOCH3 H rot 60 CH3SO2- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN H H orange 61 -C2H5 -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 -NHCOCH3 -OC2H5 rot 62 -C2H5 -COOC2H5 -COOC2H5 -C2H5 -C2H5 -NHCOCH3 H rot 63 H5C6HNCO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H rot 64 H5C6HNCO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H rot      Tabelle 2 Farbstoffe der Formel:
EMI5.1     
 Beispiel R1 R2 R'2 K Nuance auf No.

  Polyester
EMI5.2     


<tb> 65 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> HtNC <SEP> C6H5 <SEP> gelb
<tb>  <SEP> 3
<tb> 66 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> HO <SEP> N <SEP> H <SEP> gelb
<tb>  <SEP> 1
<tb>  <SEP> 3¸H
<tb> 67 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> H2N <SEP> N- <SEP> C <SEP> H <SEP> CgI95 <SEP> gelb
<tb>  <SEP> 65
<tb>  <SEP> M
<tb>  <SEP> H3 <SEP> N
<tb> 68 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> H2N <SEP> F <SEP> gelb
<tb>  <SEP> R'- <SEP> CH3
<tb>  <SEP> N
<tb>  <SEP> CH3
<tb> CH3
<tb> 69 <SEP> H <SEP> COOCzH <SEP> -COOCzHs <SEP> 3tH33 <SEP> rot
<tb>  <SEP> N1c113
<tb>  <SEP> H <SEP> 3C <SEP> CH <SEP> 2CH2 <SEP> OR
<tb> 70 <SEP> H <SEP> -COOC2H5 <SEP> -COOCHs <SEP> HC <SEP> H <SEP> 2CH2COOCH2CH2CH2CH3 <SEP> rot
<tb>  <SEP> 71 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2H5 <SEP> C <SEP> 0N0 <SEP> rot
<tb>  <SEP> X <SEP> OCH
<tb>  <SEP> 0
<tb> 72 <SEP> -C2H5 

   <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> t <SEP> C <SEP> 6H5 <SEP> gelb
<tb>  <SEP> v <SEP> 5
<tb>  <SEP> CH3
<tb>   
Tabelle 2 (Forstetzung) Beispiel R1 R2 R'2 K Nuance auf No. Polyester
EMI6.1     


<tb>  <SEP> NR2
<tb> 73 <SEP> -C2Hs <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> Nt <SEP> 5"CgHg <SEP> gelb
<tb>  <SEP> N
<tb>  <SEP> CH3
<tb>  <SEP> OH
<tb> 74 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> oY <SEP> gelb
<tb>  <SEP> CH3
<tb>  <SEP> 0{I
<tb> 75 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> 2pCH, <SEP> rot
<tb>  <SEP>  <  <SEP> CH3
<tb>  <SEP> SO2 <SEP> -N-C <SEP> H2CH2OCOCH3
<tb>  <SEP> 76 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> Nt. 

  <SEP> rot
<tb>  <SEP> s <SEP> SO,NHCM,
<tb>  <SEP> bS02NHCH3
<tb>  <SEP> 77 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2H5 <SEP> 3 <SEP> ,CN <SEP> gelb
<tb>  <SEP> 6Et-o
<tb>  <SEP> J
<tb>  <SEP> CH2CH3
<tb>  <SEP> 78 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2H5 <SEP> H <SEP> C6/4 <SEP> nu <SEP> gelb
<tb>  <SEP> bb
<tb>  <SEP> C <SEP> gil
<tb>  <SEP> 79 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> t <SEP> N2 <SEP> -CH\ <SEP> rot
<tb>  <SEP> C <SEP> -CH
<tb>  <SEP> H3 <SEP> H2 <SEP> 2
<tb>  <SEP> 80 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> V <SEP> gelb
<tb>  <SEP> CH3
<tb> 81 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> C112-CH <SEP> 24o <SEP> orange
<tb>  <SEP> -CH <SEP> -C <SEP> / <SEP> 2
<tb>  <SEP> CR2 <SEP> 2
<tb>  <SEP> OH
<tb>  <SEP> 82 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> · <SEP> gelb
<tb>   
Anwendungsbeispiel
7 Teile des nach Beispiel 1 hergestellten Farbstoffs werden mit 4 Teilen  

   dinaphthylmethandisulfonsaurem Natrium, 4 Teilen Natriumcetylsulfat und 5 Teilen wasserfreiem Natriumsulfat in einer Kugelmühle 48 Stunden zu einem feinen Pulver gemahlen.



   1 Teil des so erhaltenen Färbepräparates wird mit wenig Wasser angeteigt und die erhaltene Suspension durch ein Sieb einem 3 Teile Natriumlaurylsulfat in 4000 Teilen Wasser enthaltenden Färbebad zugesetzt. Das Flottenverhältnis beträgt 1:40. Man gibt nun 100 Teile gereinigtes Polyesterfasermaterial bei   40-500    in das Bad, gibt 20 Teile eines chlorierten Benzols in Wasser emulgiert zu, erwärmt das Bad langsam auf   100o    und färbt 1-2 Stunden bei 95-100 . Die brillant rot gefärbten Fasern werden gewaschen, geseift, erneut gewaschen und getrocknet. Die egale Färbung ist sehr gut licht-, wasch-, schweiss-, sublimier- und thermofixierecht. 



  
 



   The invention relates to a process for the preparation of azo disperse dyes.



   The new disperse dyes correspond to formula I.
EMI1.1
 wherein Rl is hydrogen, optionally substituted alkyl or phenyl or a group of the formula -COR3, -SO2R3 or -CO-NR4RI4, R2 and R'2 independently of one another hydrogen, cyano, nitro or a group of the formula -CO-R'3 or - SO2-R3, the symbols R3 independently of one another optionally substituted alkyl or phenyl, alkoxy or phenoxy, the symbols R'3 independently of one another hydroxyl or one of the meanings of R3, R4 hydrogen, alkyl or phenyl, Rt4 hydrogen or alkyl, and K denotes the remainder a coupling component of the benzene, naphthalene or heterocyclic series or from the series of compounds with an activated methylene group and the molecule is free from sulfonic acid groups.



  Regardless of the other symbols or substituents, the following are preferably: Rl is hydrogen, Cl-4-alkyl, which can carry a substituent from the group consisting of chlorine, bromine, cyano or Cl-4-alkoxycarbonyl, Cl-4-alkyl-carbonyl , Cl-alkoxycarbonyl, Cl-2-alkylaminocarbonyl, di- (C1-2-alkyl) -aminocarbonyl, Cl-2-alkylsulfonyl, Cl-2-alkoxysulfonyl or phenylsulfonyl, in particular hydrogen; R2 and R'2 Cl-2-alkoxycarbonyl or cyano, in particular Cl-2-alkoxycarbonyl;

  ; K is the remainder of a coupling component of the aminobenzene, aminonaphthalene, pyrazolone-5-, 5-aminopyrazole, pyridone, pyrimidone, phenol, naphthol, diaminopyridine, diaminopyrimidine, tetrahydroquinoline, coumarin or pyrrole series or from the Group of compounds with an activated methylene group, in particular a radical of the formula IV
EMI1.2
   Rs is hydrogen or an optionally substituted C1-alkyl radical, in particular hydrogen or a Cl-4-alkyl radical, which optionally has a substituent from the group consisting of cyano, chlorine, hydroxyl, Cl-2-alkoxy, formyloxy, chloroacetoxy, C1-alkylcarbonyloxy, Cl -2-alkoxycarbonyl, Cl-2-alkoxycarbonyloxy and benzoyloxy, especially C2-3-alkyl,

   which is substituted by cyano or Cl-2-alkyl-carbonyloxy; R6 is an optionally substituted Cl-4-alkyl or phenyl radical, in particular a Cl-4-alkyl radical, which optionally has a substituent from the series hydroxy, Cl-2-alkoxy, cyano, phenyl, phenoxy, formyloxy, chloroacetoxy, Cl-4- Alkyl-carbonyloxy, Cl-2-alkoxycarbonyl, Cl-2-alkoxycarbonyloxy, benzoyloxy, phenylaminocarbonyloxy, phthalimidyl, saccharinyl-2, pyridyl or benzthiazolyl-2-mercapto, or a phenyl radical which optionally has one or two substituents the group carries chlorine, bromine, methyl, methoxy and ethoxy, especially C2-3-alkyl, which is substituted by Cl-2-alkyl-carbonyloxy,

   or Rs and R6 together are an alkylene radical which is optionally interrupted by an -0- or -SOz bridge; R7 is hydrogen, chlorine, bromine, cyano, Cl-2-alkyl, Cl-2-alkoxy or an acylamino radical, in particular hydrogen, chlorine, bromine, cyano, methyl, Cl-2-alkoxy, formylamino, Cl-4-alkyl carbonylamino , Benzoylamino, chloro-, bromo- or phenoxyalkylcarbonylamino, Cl-1-alkoxycarbonylamino, benzyloxycarbonylamino, G-2-alkoxy-ethoxycarbonylamino or G-2-alkylsulfonylamino, especially hydrogen, methyl or Cí-2-alkyl-carbonylamino; Rs hydrogen, methyl, chlorine, bromine, Cl-2-alkoxy or phenoxy, in particular hydrogen.



   Preferably, R7 and Rs do not simultaneously denote chlorine or bromine.



   Acyl radicals in acylamino (R7) are preferably radicals of the formula RY- or R'-D, in which R is alkyl which is a substituent from the group consisting of chlorine, bromine, hydroxyl, alkoxy, cyano, phenyl, phenoxy, amino, alkyl or Dialkylamino and phenylamino or phenyl, which can carry up to two substituents from the group consisting of chlorine, bromine, methyl, methoxy, nitro, cyano and alkoxycarbonyl, Y is a radical of the formula -O-CO- or -S02-, R 'is hydrogen or one of the meanings of R, Z is a radical of the formula -CO-, -NR / 'CO- or -NR "SO2 and R" is hydrogen or one of the meanings of R, although acetals are excluded.



   Particularly suitable acylamino radicals are formylamino, alkylcarbonylamino, chlorine, bromine, alkoxy, phenyl, phenoxy or cyano-alkylcarbonylamino, alkoxy-carbonylamino, alkoxy-ethoxy- or -propoxy-carbonylamino, alkylsulfonylamino and benzoylamino, in which the benzene nucleus has a substituent from the group consisting of chlorine, bromine, methyl, methoxy, nitro and cyano, can be considered.



   Unless stated otherwise, all alkyl radicals (and also the alkoxy radicals) contain 1, 2, 3 or 4, in particular 1 or 2, carbon atoms.



   The process for the preparation of the new compounds of the formula 1 is characterized in that the diazonium compound is obtained from an amine of the formula II
EMI1.3
 with a compound of the formula III
H-K (III) couples.



   The amines of the formula II are known; B. by G. Gompper et al., Annalen 659, 90-101, (1962), described, or can be produced analogously to known methods.



   The preparation of the diazonium compounds and the coupling with the compounds of the formula III are also carried out analogously to known methods.



   The processing of the new compounds of the formula I to dye preparations is carried out in a generally known manner, for. B.



  by grinding in the presence of dispersants and / or fillers. The preparations, optionally dried in vacuo or by atomization, can, after the addition of more or less water, be used for dyeing, padding or printing in what is known as a long or short liquor. The dyes are extremely well absorbed from aqueous suspension on textile material made of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing or printing textile material made from linear, aromatic polyesters and from cellulose 2 1/2 acetate, cellulose triacetate and synthetic polyamides.



   One dyes or prints according to known, z. B. the method described in French Patent No. 1,445,371.



   The dyeings obtained have good all-round fastness properties; The light fastness, the heat-setting, sublimation and pleating fastness are to be emphasized.



   In the following examples, the parts are parts by weight and the temperatures are given in degrees Celsius.



   example 1
To a mixture of 107 parts of nitrosylsulfuric acid (prepared by dissolving 7 parts of sodium nitrite in 100 parts of concentrated sulfuric acid), 85 parts of glacial acetic acid and 15 parts of propionic acid, 31.5 parts of 3-amino-4-hydroxy-thieno [2 , 3-b] -thiophene-dicarboxylic acid- (2, - 5) -diethyl ester was added. A mixture of 85 parts of glacial acetic acid and 15 parts of propionic acid is added to the mixture obtained at 05o and the mixture is then stirred at 0-5o for 3 hours.

  A solution of 28.9 parts of N- (2'-acetoxyethyl) -N- (2'-cyanoethyl) aminobenzene in 85 parts of glacial acetic acid and 15 parts of propionic acid are then added dropwise, and the resulting coupling mixture is stirred at 0-5O for 3 hours . The reaction mixture is then poured into a mixture of 600 parts of ice and 300 parts of water with stirring, the resulting dye precipitating. It is filtered off, washed free of acid and salt with water and dried. The dye thus obtained dyes synthetic fibers in red shades with excellent fastness properties.



   The following tables show further new disperse dyes which can be prepared analogously to the procedure in the above example and the shade of their coloration on polyester fiber material.



     Table 1 dyes of the formula:
EMI3.1
   E.g. No. R1 R2 R'2 R5 R6 R7 R8 shade on polyester 2 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H ruby 3 H -COOCH3 -COOCH3 -CH2CH2-OCOCH3 -CH2CH2CN HH red 4 H -COOC2H5 -CO3CH2H5 -COOC2H5 -COOCH2H5 -COOC2H5 -CH2CH2OCOCH3 -NHCOC2H5 H ruby 5 H -COOC2H5 -COOC2H5 -CH2CH2-OCOCH3 -CH2CH2CN -NHCOCH3 H red 6 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2OCONHC6COH5-H2CH2H5-H2HOC6-CHOCH5-H2H5 -CO2HOC6-HOCH5-H2H5 -CO2HOC6H5 -CO2H5 H2HOCH5 -COOC2H5 -C2H5 -CH2CH2CN HH red 9 H -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 -NHCOCH3 -OC2H5 violet 10 H -COOC2H5 -COOC2H5 -C2H5 -C2H5 HCO2CH5 HCO2H5 HCO2-H3 H red 12 H -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 H red 13 H -COOC2H5 -COOC2H5 -CH2CH2CN -CH2CH2COOCH3 HH red 14 H -COOC2H5 -COOC2H5 -C2H5 -CH2CH2OCONHC6H5-

   15 H -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 HH red 16 H -COOC2H5 -COOC2H5 CH2CH2CN -CH2CH2OH HH red 17 H -COOC2H5 -COOC2H5 H -CH2CH2OCOCH3 H -OCH2H3 H -OCH2H3 H -OCH2 -OCH3 red 19 H -COOC2H5 -COOC2H5 H -CH2CH2OCOCH3 -NHCOCH3 Cl red 20 H -COOC2H5 -COOC2H5 H -CH2CH2OCOOCH3 -NHCOCH3 Cl red 21 H -COOC2H5 -COOC2H5 H -CH2CH2 COOCH5 -CNH2 -CO2 Cl2 -NHCOOCH2 H violet CH2OC2H5 23 H -COOC2H5 -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 -OC2H5 violet 24 H -COOCH (CH3) 2 -COOCH (CH3) 2 -CH2CH2OCOCH3 -CH2COCH2CN HH-red 25 H -CO CH3) 2 -C2H5 -CH2CH2CN -CH3 H ruby 26 H -COOCH (CH3) 2 -COOCH (CH3) 2 -CH2CH2COOCH3 -CH2CH2CN HH red 27 H -COOCH (CH3) 2 -COOCH (CH3) 2 -C2H5 -CH2CH2OCONHC6H5 - CH3 H ruby 28 H -COOCH (CH3) 2 -COOCH (CH3) 2 -C2H5 -CH2CH2CN HH red 29 H -CN -CN -CH2CH2OCOCH3 -CH2CH2CN HH ruby 30 H -CN -CN -C2H5 -CH2CH2OC6H5

   HH violet 31 H -CN -CN -C2H5 -CH2CH2CN HH violet 32 H -CN -CN H -CH2CH2COOC2H5 HH ruby 33 H -CN -CN -C2H5 -CH2CH2OCONHC6H5 HH ruby 34 H -CN -CN -CH2CH2OCCOCH3 -CH2CH2CN -N red 35 H -CON (CH3) 2 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H red 36 H -CON (CH3) 2 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN HH red Table 1 (continued) Example No.

  R1 R2 R'2 R5 R6 R7 R8 shade on polyester 37 H -CON (CH3) 2 -COOC2H5 -C2H5 -CH2CH2CN HH ruby 38 H -CONHCH3 -COOC2H5 -C2H5 -CH2CH2OCOCH3 HH ruby 39 H -CONHCH3 -COOC2H5 H -OC2H2CH2CO ruby 40 H -CONH2 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H ruby 41 H -CONH2 -COOC2H5 H -CH2CH2OCOCH3 -NHCOCH3 Cl violet 42 H -CN -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH2 -COCOCH2 -CH3CH3 HOC2H5-HOCOC2H5 -NHOCHin 43HOC2H5 -CH2CH2CN HH red 44 H -CN -COOC2H5 -C2H5 -CH2CH2CN HH ruby 45 H -CN -COOC2H5 H -CH2CH2COOC2H5 H ruby 46 H -CN -COOC2H5 H -CH2CH2OCOCH3 -OCH3 -OCH3 red 47 H -CN -COCH2H -OCH3 -OCH3 red 48 H -CN -COOC2H5 -C2H5 -CH2CH2OC6H5 HH violet 49 CH3CO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H orange 50 CH3CO- -COOC2H5 -COOC2H5 -CH2CH2CH2CH2CH3-orange -COOC2H5 H -CH2CH2COOCH3 -NHCOCH3 H red 52 CH3OCO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H

   scarlet 53 CH3OCO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN HH scarlet 54 CH3OCO- -COOC2H5 -COOC2H5 -C2H5 -C2H5 -NHCOCH3 H red 55 CH3OCO- -COOC2H5 -COOC2H5 -CH2 -6 -CH2 H2 red -CH2CH2COOC2H5 -NHCOCH 3 H red 57 (CH3) 2NCO- -COOC2H5 -COOC2H5 -C2H5 -CH3 -CH2CH2CN H red 58 (CH3) 2NCO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCOCH3 H -NHCOC2H5 scarlet 59 CH3SO2- -COOC2H5 -COOC2H5 - C2H5 -C2H5 -NHCOCH3 H red 60 CH3SO2- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN HH orange 61 -C2H5 -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2OCH5 -COOCH5 -CO2CH2OCOCH3 -CH2CH5 -CO2CH2 -OCH5 -CH2CH5 -COOCH5-H2CH2OCH5 -CH2CH5 -CH2H5 -CH2H5 -CH2H5-CO2 red 63 H5C6HNCO- -COOC2H5 -COOC2H5 -C2H5 -CH2CH2CN -CH3 H red 64 H5C6HNCO- -COOC2H5 -COOC2H5 -CH2CH2OCOCH3 -CH2CH2CN -NHCOCH3 H red Table 2 dyes of the formula:
EMI5.1
 Example R1 R2 R'2 K Nuance on No.

  polyester
EMI5.2


<tb> 65 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> HtNC <SEP> C6H5 <SEP> yellow
<tb> <SEP> 3
<tb> 66 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> HO <SEP> N <SEP> H <SEP> yellow
<tb> <SEP> 1
<tb> <SEP> 3¸H
<tb> 67 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> H2N <SEP> N- <SEP> C <SEP> H <SEP> CgI95 <SEP> yellow
<tb> <SEP> 65
<tb> <SEP> M
<tb> <SEP> H3 <SEP> N
<tb> 68 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> H2N <SEP> F <SEP> yellow
<tb> <SEP> R'- <SEP> CH3
<tb> <SEP> N
<tb> <SEP> CH3
<tb> CH3
<tb> 69 <SEP> H <SEP> COOCzH <SEP> -COOCzHs <SEP> 3tH33 <SEP> red
<tb> <SEP> N1c113
<tb> <SEP> H <SEP> 3C <SEP> CH <SEP> 2CH2 <SEP> OR
<tb> 70 <SEP> H <SEP> -COOC2H5 <SEP> -COOCHs <SEP> HC <SEP> H <SEP> 2CH2COOCH2CH2CH2CH3 <SEP> red
<tb> <SEP> 71 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2H5 <SEP> C <SEP> 0N0 <SEP> red
<tb> <SEP> X <SEP> OCH
<tb> <SEP> 0
<tb> 72 <SEP> -C2H5

   <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> t <SEP> C <SEP> 6H5 <SEP> yellow
<tb> <SEP> v <SEP> 5
<tb> <SEP> CH3
<tb>
Table 2 (forestry) Example R1 R2 R'2 K Nuance on No. polyester
EMI6.1


<tb> <SEP> NR2
<tb> 73 <SEP> -C2Hs <SEP> -COOC2H5 <SEP> -COOC2Hs <SEP> Nt <SEP> 5 "CgHg <SEP> yellow
<tb> <SEP> N
<tb> <SEP> CH3
<tb> <SEP> OH
<tb> 74 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> oY <SEP> yellow
<tb> <SEP> CH3
<tb> <SEP> 0 {I
<tb> 75 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> 2pCH, <SEP> red
<tb> <SEP> <<SEP> CH3
<tb> <SEP> SO2 <SEP> -N-C <SEP> H2CH2OCOCH3
<tb> <SEP> 76 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> Nt.

  <SEP> red
<tb> <SEP> s <SEP> SO, NHCM,
<tb> <SEP> bS02NHCH3
<tb> <SEP> 77 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2H5 <SEP> 3 <SEP>, CN <SEP> yellow
<tb> <SEP> 6Et-o
<tb> <SEP> J
<tb> <SEP> CH2CH3
<tb> <SEP> 78 <SEP> H <SEP> -COOC2H5 <SEP> -COOC2H5 <SEP> H <SEP> C6 / 4 <SEP> nu <SEP> yellow
<tb> <SEP> bb
<tb> <SEP> C <SEP> gil
<tb> <SEP> 79 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> t <SEP> N2 <SEP> -CH \ <SEP> red
<tb> <SEP> C <SEP> -CH
<tb> <SEP> H3 <SEP> H2 <SEP> 2
<tb> <SEP> 80 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> V <SEP> yellow
<tb> <SEP> CH3
<tb> 81 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> C112-CH <SEP> 24o <SEP> orange
<tb> <SEP> -CH <SEP> -C <SEP> / <SEP> 2
<tb> <SEP> CR2 <SEP> 2
<tb> <SEP> OH
<tb> <SEP> 82 <SEP> H <SEP> -COOC2Hs <SEP> -COOC2Hs <SEP> · <SEP> yellow
<tb>
Application example
7 parts of the dye prepared according to Example 1 are mixed with 4 parts

   sodium dinaphthylmethanedisulfonic acid, 4 parts of sodium cetyl sulfate and 5 parts of anhydrous sodium sulfate were ground to a fine powder in a ball mill for 48 hours.



   1 part of the dye preparation obtained in this way is made into a paste with a little water and the suspension obtained is added through a sieve to a dye bath containing 3 parts of sodium lauryl sulfate in 4000 parts of water. The liquor ratio is 1:40. 100 parts of purified polyester fiber material are then added to the bath at 40-500, 20 parts of a chlorinated benzene emulsified in water are added, the bath is slowly heated to 100o and dyed for 1-2 hours at 95-100. The brilliant red colored fibers are washed, soaped, washed again and dried. The level coloring is very good fast to light, washing, perspiration, sublimation and heat setting.

Claims (1)

PATENTANSPRÜCHE PATENT CLAIMS I. Verfahren zur Herstellung von Dispersionsfarbstoffen der Formel I EMI7.1 worin R1 Wasserstoff, gegebenenfalls substituiertes Alkyl oder Phenyl oder eine Gruppe der Formel -COR3, -SO2R3 oder -CO-NR4R4, R und R'2 unabhängig voneinander Wasserstoff, Cyan, Nitro oder eine Gruppe der Formel -CO-R'3 oder -SO2-R3, die Symbole R3 unabhängig voneinander gegebenenfalls substituiertes Alkyl oder Phenyl, Alkoxy oder Phenoxy, die Symbole R'3 unabhängig voneinander Hydroxyl oder eine der Bedeutungen von R3, R4 Wasserstoff, Alkyl oder Phenyl, R'4 Wasserstoff oder Alkyl, und K den Rest einer Kupplungskomponente der Benzol-, Naphthalin- oder heterocyclischen Reihe oder aus der Reihe der Verbindungen mit aktivierter Methylengruppe bedeuten und das Molekül von Sulfonsäuregruppen frei ist, dadurch gekennzeichnet, I. Process for the preparation of disperse dyes of the formula I. EMI7.1 wherein R1 is hydrogen, optionally substituted alkyl or phenyl or a group of the formula -COR3, -SO2R3 or -CO-NR4R4, R and R'2 independently of one another hydrogen, cyano, nitro or a group of the formula -CO-R'3 or - SO2-R3, the symbols R3 independently of one another optionally substituted alkyl or phenyl, alkoxy or phenoxy, the symbols R'3 independently of one another hydroxyl or one of the meanings of R3, R4 is hydrogen, alkyl or phenyl, R'4 is hydrogen or alkyl, and K denote the remainder of a coupling component of the benzene, naphthalene or heterocyclic series or from the series of compounds with an activated methylene group and the molecule is free of sulfonic acid groups, characterized in that dass man die Diazoniumverbindung aus einem Amin der Formel II EMI7.2 mit einer Verbindung der Formel III H-K (III) kuppelt. that the diazonium compound from an amine of the formula II EMI7.2 with a compound of the formula III H-K (III) couples. II. Die nach dem Verfahren gemäss Patentanspruch I herge stellten Verbindungen der Formel I. II. The compounds of the formula I prepared by the process according to claim I UNTERANSPRÜCHE 1. Verfahren gemäss Patentanspruch I, dadurch gekenn zeichnet, dass man Verbindungen der Formel I herstellt, worin K den Rest einer Kupplungskomponente der Amino benzol-, Aminonaphthalin-, Pyrazolon-5-, 5-Aminopyrazol-, Pyridon-, Pyrimidon-, Phenol-, Naphthol-, Diaminopyridin-, -pyrimidin-, Tetrahydrochinolin-, Cumarin- oder Pyrrolreihe oder aus der Gruppe der Verbindungen mit aktivierter Methylengruppe, bedeutet. SUBCLAIMS 1. The method according to claim I, characterized in that compounds of the formula I are prepared in which K is the radical of a coupling component of the amino benzene, aminonaphthalene, pyrazolone-5-, 5-aminopyrazole, Pyridone, pyrimidone, phenol, naphthol, diaminopyridine, pyrimidine, tetrahydroquinoline, coumarin or pyrrole series or from the group of compounds with an activated methylene group. 2. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass man Verbindungen der Formel I herstellt, worin R1 Wasserstoff, Cl-4-Alkyl, das einen Substituenten aus der Gruppe Chlor, Brom, Cyan oder Cl-4-Alkoxy-carbonyl tragen kann, Cl-4-Alkyl-carbonyl, Cl-4-Alkoxy-carbonyl, C1-2- Alkyl-aminocarbonyl, Di-(Cl-2-alkyl)-aminocarbonyl, Cl-2 Alkylsulfonyl, Cl-2-Alkoxysulfonyl oder Phenylsulfonyl, R2 und R'2 C1-2-Alkoxy-carbonyl oder Cyan, K einen Rest der Formel IV EMI7.3 Rs Wasserstoff oder einen gegebenenfalls substituierten Cl-4-Alkylrest R6 einen gegebenenfalls substituierten Cl-4-Alkyl- oder Phenylrest, 2. The method according to claim I, characterized in that compounds of the formula I are prepared in which R1 is hydrogen, Cl-4-alkyl, which can carry a substituent from the group consisting of chlorine, bromine, cyano or Cl-4-alkoxycarbonyl, Cl-4-alkyl-carbonyl, Cl-4-alkoxycarbonyl, C1-2-alkyl-aminocarbonyl, di- (Cl-2-alkyl) -aminocarbonyl, Cl-2 alkylsulfonyl, Cl-2-alkoxysulfonyl or phenylsulfonyl, R2 and R'2 C1-2-alkoxycarbonyl or cyano, K is a radical of the formula IV EMI7.3 Rs hydrogen or an optionally substituted Cl-4-alkyl radical R6 an optionally substituted Cl-4-alkyl or phenyl radical, oder Rs und R6 gemeinsam einen gegebenenfalls durch eine 0- oder -SO2-Brücke unterbrochenen Alkylenrest, R7 Wasserstoff, Chlor, Brom, Cyan, Cl-2-Alkyl, Cl-2-Alkoxy oder einen Acylaminorest und Rs Wasserstoff, Methyl, Chlor, Brom, C1-2-Alkoxy oder Phenoxy bedeuten. or Rs and R6 together are an alkylene radical optionally interrupted by an 0- or -SO2 bridge, R7 is hydrogen, chlorine, bromine, cyano, Cl-2-alkyl, Cl-2-alkoxy or an acylamino radical and Rs is hydrogen, methyl, chlorine, Mean bromine, C1-2-alkoxy or phenoxy. 3. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass man Verbindungen der Formel I herstellt, worin R1 Wasserstoff, R2 und R'2 Ci--Alkoxy-carbonyl, K einen Rest der Formel IV EMI7.4 Rs Wasserstoff oder einen Cl-4-Alkylrest, der gegebenenfalls einen Substituenten aus der Gruppe Cyan, Chlor, Hydroxyl, C1-2-Alkoxy, Formyloxy, Chloracetoxy, Cl-4-Alkyl-carbonyl- oxy, Cl-2-Alkoxycarbonyl, Cl-2-Alkoxy-carbonyloxy und Benzoyloxy trägt, R6 einen Cl-4-Alkylrest, der gegebenenfalls einen Substituenten aus der Reihe Hydroxy, Cl-2-Alkoxy, Cyan, Phenyl, Phenoxy, Formyloxy, 3. The method according to claim I, characterized in that compounds of the formula I are prepared in which R1 is hydrogen, R2 and R'2 Ci - alkoxycarbonyl, K is a radical of the formula IV EMI7.4 Rs is hydrogen or a Cl-4-alkyl radical, which optionally has a substituent from the group consisting of cyano, chlorine, hydroxyl, C1-2-alkoxy, formyloxy, chloroacetoxy, Cl-4-alkyl-carbonyl oxy, Cl-2-alkoxycarbonyl, Cl -2-alkoxy-carbonyloxy and benzoyloxy, R6 carries a Cl-4-alkyl radical, which optionally has a substituent from the series hydroxy, Cl-2-alkoxy, cyano, phenyl, phenoxy, formyloxy, Chloracetoxy, C1-4-Alkyl-carbonyloxy, Cl-2 Alkoxy-carbonyl, Cl-2-Alkoxy-carbonyloxy, Benzoyloxy, Phenylaminocarbonyloxy, Phthalimidyl, Saccharinyl-2, Pyridyl, oder Benzthiazolyl-2-mercapto trägt, oder einen Phenylrest, der gegebenenfalls ein oder zwei Substituenten aus der Gruppe Chlor, Brom, Methyl, Methoxy und Äthoxy trägt, R7 Wasserstoff, Chlor, Brom, Cyan, Methyl, Cl-2-Alkoxy, Formylamino, Cl-4-Alkyl-carbonylamino, Benzoylamino, Chlor-, Brom- oder Phenoxyalkylcarbonylamino, Cl-2-Alkoxy- carbonylamino, Benzyloxycarbonylamino, Cl-2-Alkoxy-äth- oxycarbonylamino oder Cl-2-Alkylsulfonylamino und Rs Wasserstoff, Methyl, Chlor, Brom, Cl-2-Alkoxy oder Phenoxy bedeuten. Chloroacetoxy, C1-4-alkyl-carbonyloxy, Cl-2-alkoxy-carbonyl, Cl-2-alkoxy-carbonyloxy, benzoyloxy, phenylaminocarbonyloxy, phthalimidyl, saccharinyl-2, pyridyl, or benzthiazolyl-2-mercapto, or a phenyl radical which optionally carries one or two substituents from the group consisting of chlorine, bromine, methyl, methoxy and ethoxy, R7 hydrogen, chlorine, bromine, cyano, methyl, Cl-2-alkoxy, formylamino, Cl-4-alkyl-carbonylamino, benzoylamino, chlorine , Bromo- or phenoxyalkylcarbonylamino, Cl-2-alkoxycarbonylamino, benzyloxycarbonylamino, Cl-2-alkoxy-ethoxycarbonylamino or Cl-2-alkylsulfonylamino and Rs are hydrogen, methyl, chlorine, bromine, Cl-2-alkoxy or phenoxy. 4. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass man Verbindungen der Formel I herstellt, worin R1 Wasserstoff, R2 und R'2 C1-2-Alkoxycarbonyl, K eine Kupplungskomponente der Formel IV EMI8.1 Rs C2-3-Alkyl, das durch Cyan oder C1-1-Alkyl-carbonyloxy substituiert ist, R6 C2-3-Alkyl, das durch C1-2-Alkyl-carbonyloxy substituiert ist, R7 Wasserstoff, Methyl oder C1-2-Alkyl-carbonylamino und Rs Wasserstoff bedeuten. 4. The method according to claim I, characterized in that compounds of the formula I are prepared in which R1 is hydrogen, R2 and R'2 are C1-2-alkoxycarbonyl, K is a coupling component of the formula IV EMI8.1 Rs C2-3-alkyl which is substituted by cyano or C1-1-alkyl-carbonyloxy, R6 C2-3-alkyl which is substituted by C1-2-alkyl-carbonyloxy, R7 hydrogen, methyl or C1-2-alkyl -carbonylamino and Rs are hydrogen.
CH869976A 1976-07-07 1976-07-07 Azo dispersion dyes contg. thiophene gps. CH603750A5 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0251114A2 (en) * 1986-07-02 1988-01-07 BASF Aktiengesellschaft Thienothiophene dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0251114A2 (en) * 1986-07-02 1988-01-07 BASF Aktiengesellschaft Thienothiophene dyes
EP0251114A3 (en) * 1986-07-02 1988-03-09 Basf Aktiengesellschaft Thienothiophene dyes

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